“The merchants who trust us most are the ones we trusted first.”
Ciera Maguire, Product Manager
- 01
What's the biggest shift in how you work over the last year?
I used to write specs in documents that sat in Confluence until engineering read them. Now I write machine-readable specs that feed directly into agentic development pipelines. The spec is not a communication artifact anymore — it's an executable input. That changes how precise you have to be, and it makes the vagueness in your thinking visible immediately.
- 02
Walk me through a problem you solved using AI that you couldn't have tackled the same way before.
We had a merchant onboarding drop-off problem that nobody could quantify clearly. I ran an LLM over six months of support chat transcripts to categorize and cluster friction points. What came back was a taxonomy of seventeen distinct onboarding failure modes, ranked by frequency. We prioritized the top three, built fixes in two sprints, and drop-off rate fell 22% in thirty days. The analysis that enabled that would have taken a quarter manually.
- 03
What do you wish you'd known before joining?
That speed is a feature of the culture, not just the technology. Decisions get made fast here. If you're used to building consensus over weeks, that pace will feel abrupt at first. Once you calibrate, you realize it's not recklessness — it's that people trust each other's judgment enough to move. That trust is earned and real.
See open seats.
Building across engineering, product, data, sales, ops, finance, and people. Every role is an Operator role.
We get people offline through quality local experiences at great value. That's still the mission. Everything above is what it takes to deliver it in 2026.